Now or Next: Mid-Life Career Choices and Applying Strategic Thinking To Your Personal Life

Lately, my LinkedIn has been slammed with multiple versions of “don’t choose your next job, choose your next boss.” For my clients (or my children) in their mid-twenties, this advice is sage. At that early point in your life you are trying to grow into your passion while defining a path to get there. A boss that can be part of that journey is invaluable. But increasingly as my clients look more like me (and that is not in my mid-twenties) I find the thought of “choosing a boss” to be more of a Don Quixote-ish meme that I find lovely “thumbs up” to but would not advise them to do. Now, I’m not suggesting you sign up to work for Darth Vader, I simply believe the work you choose to do in mid-life/career should be less about who you can learn from and more about who and what you can teach.

Regardless of whether it’s a boss or a job, what is important is that you choose it.

Choice implies purposeful decisions between at least two alternatives. To choose well you need a disciplined approach – one that mirrors how organizations think about their strategic choices. A process like the one pictured below helps you know what to say “yes” to and what to avoid like the plague. The visual below shows the steps in this process and forces us to think about ourselves, our gifts, and our ambitions so that the choice becomes more self-evident.

4 questions to guide career path

What are my goals and aspirations for my career and life? Answering this is a little like rethinking “who do I want to be when I grow up?” At its core this requires as much a deep reflection on who have I been, what are the critical events that have built who I am and what have I taken from each of these. I often have clients start this journey by writing a set of “stories from their past” – tell me a story when you overcame great odds and successfully led/implemented something. Recall a story when you have brought together a B-team and achieved great results. Share the prose of when you faced your greatest struggle in career and weren’t successful. Give me a story about when you were at your absolute best in in work or other leadership. Rather than being a self-serving set of “wasn’t I great?” reminders, the patterns in these stories reveal our values, how we have grown, and what we have a lasting passion for.

In writing these stories, we also discover what we have a passion to teach. At this point in career the desire to impart wisdom, rather than soak it up, becomes as instinctual as migrating south for the winter. Reconnecting with the events, experiences and reflections that have shaped your stories makes it clear where you can teach and advise others.

In which markets/roles should I compete? For our clients exploring business opportunities its shocking how many of them would answer this with “we’re already in markets” as opposed to evaluating the strategic value of where they are and whether there exists a path for growth, Again the “I’m already doing this job so I should just want the next level up of it” isn’t choiceful – it is inertia. I’ve never worked with a successful CEO who ended up there by chance. Do I want to work in a public setting or private? Am I great in start-ups or mature organizations? Am I better in turn-arounds or high performance teams? Do I continue my technical depth and expertise or leverage my leadership? These are the kinds of “market facing” questions you should be asking as you consider your next job. This purposeful choice around the market you’ve been successful in describes the students and classroom you can teach in.

How will I position myself to serve? Once defining what you are most passionate about and identifying the market that would benefit from that passion, you need to put together a value proposition that is externally viable. It’s great if you know where you want to go, but if no one else sees you as an expert in that industry or adding value in that space, you’ll have an uphill battle. You need to have a very clear elevator speech on how you are differentiated from your competition, what is your primary source of value, and how would you (in that role or opportunity) provide an advantage for whoever hires you. So rather than simply making a case for what you’ve done in the past, frame your past successes as lessons learned that you can impart on others.

What essential capabilities must I leverage or build to win? I find that my favorite teachers or authors are clear on their expertise and refused to pretend like they were a know it all guru. The further you get in your career the clearer you become on the few things you truly know. As you are considering your next position, and the opportunity to share the deep knowledge that you’ve gathered, you’ll want to position what you know and do best. However, getting to a meaningful next position also requires a very rigorous and candid look at what you are missing. Optimally filling those gaps is the best strategy but at a minimum, having a clear understanding of why you have gaps in knowledge or experience and how you compensate for them (e.g. building a team around you) will act as a confirmation of the expertise you do bring.

In the later years of your career you may find it very difficult to find the perfect organization or boss that will catapult your career. Recognize it for what it is: a sign that you no longer need a boss that will shape your future, you have an opportunity to be the boss that shape other’s futures.

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About

Mindy Millward

With over 25 years of experience as a veteran business advisor, Mindy has worked with a range of leaders including CEOs of Fortune 500s. Her goal is to help them and their firms navigate significant transitions in shifting strategy, redesign organizations, and deliver increased performance.

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